Hydrochloric Acid → HCID 10194952, compound

HRID 1582138Notes

Reaction equation

HRID 1582138 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][N:28]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[C:17]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[CH:16][CH:15]=[C:14]([O:24][CH3:25])[C:12]=2[N:13]=1)=[O:7].Cl.[C:30](OC(=O)C)(=[O:32])[CH3:31].C(=O)(O)[O-].[Na+]>C1COCC1.O.C(N(CC)CC)C>[C:30]([N:21]1[CH2:20][CH2:19][CH:18]([C:17]2[C:11]3[S:10][C:9]([NH:8][C:6](=[O:7])[C:5]4[CH:26]=[CH:27][N:28]=[C:3]([O:2][CH3:1])[CH:4]=4)=[N:13][C:12]=3[C:14]([O:24][CH3:25])=[CH:15][CH:16]=2)[CH2:23][CH2:22]1)(=[O:32])[CH3:31]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 227195582-methoxy-N-(4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-isonicotinamide

Product 1

HCID 10194952HCID 10194952, compoundYield 74.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 0.07 g (0.16 mMol) 2-methoxy-N-(4-methoxy-7-piperidin-4-yl-benzothiazol-2-yl)-isonicotinamide 1:2 hydrochloride in 4 ml THF were added 0.049 ml triethyl amine. At 0° C. 0.018 ml (0.11 mMol) acetic anhydride was added dropwise and stirred for 1 h. Then a mixture of 5 ml sat. aqueous sodium bicarbonate and 10 ml water were added. This was extracted three times with 15 ml ethyl acetate, the combined organic phases were dried over sodium sulfate and evaporated to dryness in vacuo. One obtained 0.036 g (51%) N-[7-(1-acetyl-piperidin-4-yl)-4-methoxy-benzothiazol-2-yl]-2-methoxy-isonicotinamide as a white solid. F.p.: 242-244° C.

Workup

  1. customAt 0° C
  2. additionwere added
  3. extractionThis was extracted three times with 15 ml ethyl acetate
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-e0aa20f9068c4a9bb5331ca4b055b8cf
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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